The Deepest Dive: A New York City Pub Crawl to End All Pub Crawls

Since time immemorial, dive bars have occupied a very special place in the hearts of booze-inclined New Yorkers. We love dive bars because, much like the city itself, they’re unique, oozing with comforting familiarity and a genuine sense of authenticity–or at least oozing with something. Each dive demonstrates its own spin on a common theme, from perpetually disgusting bathrooms and two ingredient cocktails to $3 bottles of Bud heavy, shoddy jukeboxes and salty-sweet bartenders. Stepping into one of these joints instantly transports you back to a smoky, sepia-toned, pre-Disneyfied New York City, an era many of us can only recall from the vantage point of a child no higher than the grimy bar top we happily rest our elbows on today. With their gritty charm and undeniable character, these little relics have the power to delight even the poshest of city dwellers and the snobbiest of beer geeks.

For my last birthday, my good friend (and number one drinking buddy) gifted me a thin book lovingly titled New York City’s Best Dive Bars: Driving and Diving in the Five Boroughs by Wendy Mitchell. A twelve-year-old hand-me-down from a regular at her bar, the dedication page reads “For all my favorite drinking buddies, you know who you are.” It’s enough to make heartfelt tears drip into your 7 & 7. Though just over a decade old, Mitchell’s guide is already showing its age–a heaping handful of the 90 NYC bars profiled are dead and gone, victims of clean streets initiatives, rapid gentrification and the ever-present Florida retirement draw.

Despite these fallen soldiers, a healthy number of trusty dives remain tucked away throughout the city, each fighting the good fight against impending $18 bespoke cocktails and Starbucks-style Irish pubs. Enough, in fact, to constitute a pretty killer pub crawl. Without further ado, I present you roadmap to a debaucherous traipse through the New York City of yesteryear. These dives may hail from vastly different neighborhoods and cater to a broad range of clientele, but together they make up the suds-soaked murmuring heart beat of a city where everybody might know your name, but nobody really cares. Pull up a stool and strap on your drinking cap, this one’s going to be a doozy.

Note: Dive bar allegiances are extremely personal, and I in no way claim that this list represents a definitive “best of,” but rather one drinker’s proven route for a down and dirty good time.

Other Note: I’m not entirely sure it’s possible to hit each of these gems in one fell swoop, but if you attempt it, I’d recommend doing it slowly. Stay hydrated, soldiers.

1) Jimmy’s Corner (140 West 44th Street, between Broadway & 7th Avenue)
I simply love this friendly, boxing themed hideaway smack dab in the middle of the city’s most stressful district. It’s narrow, it’s long, the jukebox is always jumping and the Bud is always freezing cold, not to mention $4 Jamesons, sports on the tube and the sweetest waitresses you’ll ever meet. Enough said.

2) Rudy’s Bar & Grill (627 9th Avenue between 44th & 45th Streets)
Most of these places don’t serve food (it’s probably for the best) so load up on free hot dogs at your night’s second stop, a famous 9th Avenue dive who’s just a tad too in on it’s own joke, but a fun spot all the same. It was awarded one of the city’s first post-Prohibition liquor licenses, and the original furnishings are straight out of Scorsese’s central casting. Whatever you do, don’t try to steal the six foot pig statue at the front door — they bolted that sucker down years ago.

3) Holland Bar (532 9th Avenue between 39th & 40th Streets)
“Amateurs take note,” Mitchell’s entry on this Port Authority dive begins, “The Holland Bar prides itself on being a real drinker’s bar, so you may have to engage in tolerance training before you even step in the door.” With enough Rudy’s hot dogs in your belly, you should be plenty game to pop in here for a cheap mixed drink or a shot of well liquor (no top shelf here, fellas). And speaking of fellas, this dingy watering hole is a man cave, for sure. “One of the guys quipped this could be a gay bar because it’s always so full of men,” Mitchell continues. “(It’s most certainly not, though).”

4) Billymarks West (332 9th Avenue between 29th & 30th Streets)
By this point, you’ll want to relax, so kick back with a High Life at this nondescript North Chelsea dive that, with its drop ceiling and lack of draft beer exudes a pleasantly homey suburban rec room vibe. Owners Billy and Mark (of course) are easy with the jokes and heavy with the shots and the pool table should keep you happily occupied for quite some time. Don’t get too comfy, though — the night is young and there’s much more filthy fun yet to come.

Optional – 5A) Julius’ (159 West 10th Street between 7th Avenue & Waverly Place)
Still hungry? This next optional pit stop will solve all your drunk muchy problems with their world famous cheeseburger, a patty so juicy and satisfying that it confidently takes the Village’s reigning burger champ, Corner Bistro, to task. Julius’, one of the oldest gay bars in New York City, has truly seen it all and the cast of diehard regulars tell some of the best stories you’ll ever hear. If you’re game, saddle up to the beautiful original wooden bar and soak it all in.

6) Doc Holiday’s (141 Avenue A between E 9th Street & St. Marks Place)
I’m actually not a huge fan of Doc Holliday’s, but people seem to like it and it’s a natural stop between Julius’ and Brooklyn. The beer is cheap and good — they even have Shiner Bock these days–the crowd is boisterous, the bartenders are refreshingly nice and the cowboy boots tacked to the ceiling do add a touch of Southern charm. Oh, and Big Buck Hunter–that’s an important feature. Just grab one to say you did and then hightail it across the river, pardner.

7) Melody Lanes (461 37th Street at 5th Avenue, Brooklyn)
I have a soft spot in my heart for old school bowling alleys, with their nasty shoes, sticky bowling balls and God-awful food. But don’t worry–we’re not here to play, we’re here to drink, and Sunset Park’s Melody Lanes takes it to a whole new level with a top tier dive bar manned by a bartender known far and wide for his metaphysical musings and excellent, excellent style (fluffy mutton chops, red bow tie, green suspenders–all day, every day). Now that you’re back in the good borough, settle in to the centralized, circular bar and let barman Pete Napolitano crack you a cold one.

8) Freddy’s Bar (627 5th Avenue btwn 17th & 18th Streets, Brooklyn)
Freddy’s is my neighborhood dive, a dependable if oddly designed hovel featuring a a not-too-shabby draft list, an old TV playing strange, often spooky mashup videos on loop and more than a few dark corners primed for a quick make out–this is stop eight, after all. Check the bar’s calendar to see if your visit coincides with some well curated live comedy, grab a cocktail and heckle your drunk little heart away (just don’t tell them I sent you).

9) Sunny’s Bar (253 Conover Street between Reed Street & Beard Street)
No pub crawl worth its salt could leave out Sunny’s, Red Hook’s long-running dive known for its unfalteringly loyal Brooklyn following. A few years ago, old Sandy almost took this one out, but, lucky for you, Sunny’s is back on its feet and more kitschy than ever, with polished up knick-knacks, strong drinks and lively bluegrass jams on any given night. Stepping into Sunny’s feels like coming home, like being wrapped in a big, warm, smelly hug. Trust me, it’s worth the hike.

10) Montero’s Bar & Grill (73 Atlantic Avenue at Hicks Street, Brooklyn)
Make sure to schedule your crawl on a Friday so you can take advantage of New York City’s very best karaoke night (that’s right, I said it). MC Amethyst is the queen of the dive bar serenade, even calling herself up to the mic to bring the house down with a passionately belted Broadway ballad from time to time. Montero’s is a nautically themed piece of heaven, with year-round Christmas lights illuminating dusty model ships and aging life preservers hanging from the rafters. It’s also always brighter than you remember–the makings for an ideal pub crawl closer. Stop here, sing your little heart out and then slip home to sleep it all off. You earned it.